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I mentioned at the end of my recap of the sail to Annapolis that I had some pondering to do regarding next steps. That may come as a surprise to those who read my recent post laying out my plans for this fall and winter. Namely: heading to Annapolis, then down the Chesapeake and then, in November, heading offshore with the Salty Dawg Rally to Antigua. “Life is now,” I wrote, and I was emphatic in my declaration(s).

Well, the journey south last week has given me pause, and I am now having some second thoughts about my plan to go offshore. It’s not that I don’t think Further can handle the trip. Quite the contrary: the boat is bomber, made to go offshore fast and in comfort. And it’s not that I don’t think I can handle the trip, though I will say that I have more faith in the boat than I do in myself. But last week’s trips shed some light on certain aspects of both me and Further than have me, well, pondering.

As for Further, again, she’s solid. The hull and rig are made to go, even in the lousy conditions we endured last week. But some of the auxiliary aspects on board the boat are a concern.

For instance: the dodger, the canvas “windshield” that sits at the front of the cockpit keep that area relatively dry is a shambles. That’s not a big deal—Magellan and Capt. Cook circled the globe without a dodger—but not having a dry spot from which to handle the boat is a drag and can be a safety factor when it comes to fatigue over time. I’ve looked into replacing it since last spring but canvas workers both here in Annapolis and back home in Newburyport were too swamped to take on the job and they still are.

And my jib is showing signs of wear and tear. Do I really want to get down to the islands and have my jib explode? That would suck, to put it mildly. Now, I read about sailors down there making do with jury-rigged sails after they lose a mainsail or headsail and can’t afford a replacement, but is that really how I want to tour the Caribbean?

Similarly, after last week’s fun and games, I’m kinda thinking I’d like to have a smaller jib at the bow of my boat. It makes no sense to have a sail, as I do now, that is reefed 90 percent of the time you use it. Better to have a sail sized properly for the prevailing conditions—and be a little under-gunned at times, then to be putting undue stress on your primary driver. But getting a new sail made is not going to happen in the time frame I’m dealing with, never mind the fact that I don’t have the money for a new jib.

There are also a whole host of little items that, taken together, make things a pain in the ass when the going gets tough. I still can’t seal the windows in the cabin top so they leak a bit when taking on heavy water; the hatches on the foredeck also seep a bit; the one fridge is such an energy suck that I wonder if the electrical system could keep up its needs in the hot climate of the Caribbean (another fridge works fine) without having to run the engine (and thus burn diesel which costs money) all the time.

And then there’s the fact that I still only have a year under my belt with Further. What is there on board that is on the verge of giving up the ghost and, since I don’t have a lot of time with her, I won’t know it’s coming until I get out of the country? Maybe I need more time to really know her inside and out?

Again, at her core, Further is a beast. A fast, beautiful beast made to go to sea. But all those side items add up to make me nervous sometimes. Like, say, in the middle of last week’s tumult.

As for me, well, I’ve been offshore. Several times. And I’ve been in some bumpy water and relatively high winds. But I’ve always done so as crew, never as captain. And going offshore as captain is a whole other ballgame, as I learned last week. And what I learned is this: I can’t do it alone. And not just any crew will do. I need people on board I can trust and in whom I have complete confidence. Last week’s crew, Capt. Ed, is one such person. But as last week showed, two is not enough. At least not yet in my captaining experience, anyway. Someday, I hope to be just two on board: me and my significant other. And we’ll know each other—and the boat—so well that we can handle everything thrown our way. But until that time, I need a few experienced and/or game folks along for the ride (three other people would be optimal). And they’re hard to find.

I’m on a couple of crew-finding websites and several people have expressed interest. Some of them are experienced sailors and quite intriguing. But I don’t KNOW them, so I’m wondering about how much confidence and faith I can have in someone I don’t know, especially if we’re five days into a 10-day offshore passage and the weather turns to shit.

And then there’s the ongoing question in my mind, one I’ve raised before: namely, do I want to go on such an adventure alone? Let’s say I find decent crew for the rally south; once I’m there and they all head back to the mainland, I’m on my own. I’m sure I can handle the boat in that situation, but do I want to? As much of a hermit as I can be, that might be biting off more than even I can chew. Wouldn’t it be so much better to have someone along to share the fun? Even if I had several friends come visit over the course of the winter, wouldn’t it be better to have someone equally invested in and excited by such an adventure?

So this is what weighs on my mind in the wake of last week’s trip through the rinse cycle of a washing machine. And it is these things I will ponder in the coming days here in Annapolis.

Fortunately, there are alternatives available to me. Maybe Further and I will motor our way down the Intracoastal Waterway (after the water in the Carolinas clears up in the wake of hurricane Florence) and spend the winter in Florida. The Bahamas are an easy jaunt from there and I’ve long wanted to go back to the Florida Keys, a place I’ve not been to since I was a little kid. And I hear great things about places in between: places like Charleston and Savannah and such. I could spend some time exploring and adventuring in a place where there are resources readily available and not have to venture offshore for a week-plus.

Maybe I’ll stay in Annapolis another winter, only now that I know the area and the scene and the Chesapeake better, I can build more experience all winter long AND use the town’s yachting resources to address those items aboard Further I listed above. And, in fact, I mentioned in a post script in my “Life Is Now” column that there’s a job opportunity that very much intrigues me. Well, it’s in Washington, D.C., and if that should pan out, staying in Annapolis would be a great way to resume my career AND keep building up my boat-management chops AND be in a place that I very much enjoy and where I have friends and a good life. I’ll be exploring that possibility while I’m here; I’d appreciate it if you’d cross your fingers for me on that one.

So, yeah. There is much to ponder. It all seemed so clear a couple of weeks ago, but a tumultuous jaunt across a couple hundred miles of Atlantic Ocean last week jostled that clarity quite a bit. Stay tuned for the next installment…

Well, we made it. Further and I are back in Annapolis. And it was an illuminating journey—on both the positive and negative sides. “It was the best of times, it was the worst of times,” to coin a phrase. To be honest, this writing reflects how exhausted I am following this trip. But I’ll get this recap out there and then, later, when I’ve had time to digest things a bit more, I’ll publish more thoughtful reflections on the experience. In the meantime, come along with me aboard Further as we head back to Naptown…

Day One
It just goes to show what having expectations does to you. Because to be honest, day one was a bummer. And I had expected a great kickoff to Further’s trip south.

Heading out the Merrimack River. That whitewater exploding on the north jetty should have been been a warning sign.

We topped off the diesel tank in Newburyport and were outbound around 12:55 p.m. That was later than I had planned but not by much. And when we got the mouth of the Merrimack the tide had just peaked, so the sea state was actually rather mellow. Yeah, Further had to climb over a couple of large swells but none of the waves were breaking so all was cool. And there was wind AND from a good direction: it was blowing from the southwest at around 20-plus so we unfurled the headsail and off we went. We rolled the sail back in a bit to make it smaller because it was obvious we were overpowered. And in just a couple of minutes it was clear we were still overpowered: some of the gusts were well into the 30s. So we rolled the jib away and proceeded on under engine—which we would have done as we rounded Cape Ann around 3:30 p.m. because now the wind was right on our nose.

And into that wind—and the waves they created—we plowed. Man oh man, we got beat up. We banged into a lot of waves that pretty much stopped us in our tracks, and I’d listen as I could feel the propeller get us going again. And I had often told others about how well Further handled the ocean (which she did again today), but I usually remarked that unlike other boats, Further never slammed into or coming off of waves. Well, today she slammed. A LOT. Lying in my bunk in the forward cabin was frightening when some of the slams made me feel as though the ocean was coming right through the hull. And with every one of those slams, seawater exploded over the boat, soaking the decks and even soaking the cockpit.

But the real bummer was that I reverted to my old form and was not feeling well. In years past I would always get sick the evening of the first day at sea. I’d usually barf up dinner and be sluggish overnight and by morning I’d be all better. But over time that tendency had diminished, and recent outings had been complete pleasure. But today? Man, oh man. I was not good. I wasn’t incapacitated or anything. I could get things done and even go below (usually the kiss of death if you’re feeling seasick), but I wasn’t in tip-top shape. Oh, there were a couple of wonderful moments—the lone dolphin who appeared beside the cockpit for a moment, the bioluminescence in the water sometimes sliding down Further’s deck after a wave doused the boat. But more than anything it was just uncomfortable and exhausting trying to bash our way into strong winds and seas. Fortunately, Capt. Ed was along as crew and he held down the fort when it was my turn to rest.

At some point during the trip, Further must have slammed really hard because the bolts holding the two support crosspieces for the solar panel on the davits sheared off. I noticed this as we were about to enter the Cape Cod Canal—at the same time we heard National Weather Service warnings of a line of strong thunderstorms across Rhode Island and southeastern Massachusetts, thunderstorms that were packing 40-plus-knot winds, heavy rain and a lot of lightning. I secured the solar panel crosspieces with zip ties and we boogied through the canal. Just beyond Mass Maritime Academy we turned to starboard (right) and into the little cove in Onset where we had stopped in when coming north back in July. We anchored and awaited the tumult.

Which never came. The storms apparently all passed to our north and we remained safe and snug in our little cove. As exhausted as we were, we decided to sit tight and each get a couple of hours of sleep. Which we did. And we awoke on Thursday to brisk northerly winds.

Days Two and Three
What a difference a day makes. At least at the start. We woke up in a nice, peaceful anchorage and shoved off into Buzzards Bay amid steady winds from the north and clear skies. And southwest down the bay we ran, riding the winds and grooving on the day. A couple of boats here and there but otherwise, it was just us heading south.

The wind shifted a bit to the northeast—right on our stern—so we veered toward the west a bit to keep the headsail full. As we neared Block Island we gybed over to a port tack and headed pretty much due south—again, to help the northeast winds keep the sail full and pulling. And on into the evening we headed out into the Atlantic, and around 7 p.m. we rolled the headsail in a bit since nightfall was upon us and we wanted to lessen the rolling a bit (we hoped).

Still pretty chill exiting Buzzards Bay. In a little while though…

A lovely night settled in over us, complete with moonrise and a magnificent Milky Way cascading across the sky. Sadly, it didn’t last as overcast soon enveloped the sky while the seas continued to build. And frankly, with just the two of us, it was pretty tiring. We’d take turns for an hour or two, however much we felt we could handle, in charge. That meant steering a bit, monitoring the autopilot when it was able to handle the seas, keeping us on a heading where the sail was full but also trying to keep the wave motion not so rolly that the sail fluttered and gybed around the forestay. Oh, and also keep us moving in the general direction of Cape May, N.J.

The problem is that the autopilot can’t really handle rolly seas. It wants to keep the boat on a specific angle to the wind. But with the lumpy seas trying to drive the boat one way or the other away from that angle, the autopilot freaks out and shuts down. So we steered by hand as much as we could, each in our own time. It was exhausting and frustrating, and only getting worse as time went by—so much so that around midnight we doused the sail and fired up the diesel. That way we could set the autopilot tuned to a course heading and simply worry about keeping the boat moving in the right direction.

Ed and I took turns sleeping and driving and got through the night, continuing more or less on our way. And during the morning of the third day, the strong northeast winds that had continued building the seas began to shift. At first they moved to the east which was a welcome change. And if they’d stayed in the east or even southeast we could have rolled out the jib and sailed more or less a nice reaching course toward Delaware Bay.

But no. The winds quickly clocked around until they were—you guessed it—southwest and right on our nose. In fact, we expected that to happen based on the National Weather Service forecasts we were listening to, which predicted southwest winds. But we also expected some relief since the forecast had also predicted the winds would drop to 5-10 knots. While still on the nose, such winds would have meant the seas would ease and we could make nice progress, albeit under power. Instead, the misery built as the winds not only continued out of the southwest all day, they built until they were in the mid- to upper-20s, with gusts into the 30s.

And the seas. Ugh. We had good-sized, long-period swell running up from the southeast; bouncy, short-period waves from the northeast winds we’d recently been riding; and the in-the-moment tumult from the today’s strong winds that also drove spray exploding over every inch of the boat. Further lurched over some big waves and slammed into others, while also getting rolled from side to side by the swell, and also while getting her tail pushed from side to side by the following northeasterly waves. AND we were still under power rather than sailing.

In short: it sucked. By Friday afternoon we’d been stuck in the rinse cycle of a washing machine for a good 18 hours, getting soaked, tossed around and bashed from every direction. It didn’t help my condition, which had improved over the course of the second day, and frankly, it got so bad that I was having some really unpleasant thoughts about my suitability for going forward with this whole sailing/adventure thing (more on that in a later post…maybe). Eighteen fucking hours of misery. And nothing to do but to push on through.

Which we did. And thankfully, my father was right when he said he’d never seen the storm that hadn’t passed. The forecasts that kept telling us that things were improving actually started to resemble what we were seeing all around us. The wind DID move from the southwest to the northwest and the north. The wind DID finally start to ease. With that change, the seas DID start to calm and soften. And ultimately, the overcast DID lift and leave clear skies behind…

The seas have finally chilled out enough that the amazing sunset can be enjoyed to the full.

….but not before leading to yet another sublime evening at sea. Still about 30 miles off Cape May, the sunset painted the retreating clouds in bold swatches of yellow then orange then red. And after the sun had gone west for the night, the canvas of overcast dissipated and a clear sky of stars engulfed Further, a lone ship on a now-calming sea of black beneath a even larger sea of black dotted with countless points of light. Jupiter, Saturn and Mars from west to east. Continuing beyond the red planet, a huge orange moon rising from the sea. To the distant south, lightning flashes from storms well beyond the limit of eyesight exploded like strobe lights on horizon. It doesn’t get any better than that, and all those unpleasant thoughts were replaced with the ecstasy that comes from being in the wild places on this planet.

Day Four

Early morning sailing up Delaware Bay. William Penn would have been proud.

The overnight run up Delaware Bay continued the previous evening’s transition to sublimity. An inky black surface bore Further north and the commercial traffic usually so prevalent on this stretch of water was remarkably light. There were even a couple of other sailboats working their way upstream alongside Further. We were rolling along and a gorgeous morning showed us autumnal light and colors on the shore, a bald eagle on navigation marker and warming sunshine drying out the humid air. I cooked a hearty breakfast—the first meal I’d had since the breakfast sandwich at the coffee shop in Newburyport the day we left. I cranked a little Beethoven and the morning seemed perfect.

And then I looked at the fuel gauge. All that bashing into heavy seas and headwinds meant the engine was working extra hard, and instead of burning 1.1 gallons of diesel to go six or seven miles an hour, it must have been burning a lot more per hour to go not as far. We were down to reserve levels of fuel—and the next chance for a fill-up was on the Chesapeake and Delaware Canal several hours ahead. To be honest, I didn’t know if we’d have enough diesel to get to a fuel dock; I didn’t have a lot of faith in the fuel gauge to begin with. But we were up a creek both literally and now figuratively.

So off went the engine and up went the sails. And to be honest, it was actually really cool. I dug the fact that we weren’t sailing because we wanted to, we were sailing because we HAD to. Plenty of sailors fire up the engine rather than tack upwind, and plenty of others tack just to show they’re “real” sailors and wouldn’t deign to use an engine (even though they could). But we were screwed: we didn’t really know how much fuel we had and we needed enough to get us far enough into the C&D Canal to the fuel dock, so we had to sail and that was that. As with yesterday’s tumult at sea, there was nothing else to do but push on through.

At times, the wind dropped to almost nothing. At one point, the catamaran we’d motored past overnight while they sailed had now fired up her engine and motored past us. I was getting nervous and then a fabulous bit of wind appeared: we gained a ton of ground on one tack all the way to the eastern shore, just below the nuclear power plant on the New Jersey side. We tacked over and started back toward the western shore…and the wind died completely. Well, now we were stuck. Down came the sails and back on went the engine and straight upstream we motored. Slowly. At low RPMs. Into the C&D Canal we turned, still motoring painfully slowly but, we hoped, at a low enough fuel consumption that we could reach Chesapeake City and refuel.

“Love that Dirty Water” is a song about Boston, but it could apply to the Chesapeake Bay this summer. Logs and other debris are everywhere. Caution is advised.

It was a long couple of hours but we turned a final bend and there was the bridge at Chesapeake City. We’d made it. Now to tie up to Schaefer’s fuel dock and chug some diesel. But wait! The current that hadn’t materialized to help us along to Chesapeake City was now running full force, and the same catamaran from the Delaware occupied a big chunk of the fuel dock. On my first attempt the current was too strong for me to risk squeezing into the lone gap between the cat and a string of boats also tied up, so I went downstream and turned back, planning to wedge into the gap going upstream. That also meant quickly moving the SUP and surfboards I had in a rack on the port side out of the way (and removing the rack) so we could tie up port-side-to. Meanwhile, Saturday afternoon traffic was raging all over the canal at Chesapeake City and I kept hoping the fumes we were running on held out.

Almost there…sunset on Chesapeake Bay.

Ed switched the lines and fenders to the port side, I removed the boards and rack, and we headed toward the dock. And you know what? I stuck the landing. Absolutely nailed it. I was scared shitless about the attempt—the current was strong and the dock was packed—but I was proud of the spot into which I squeezed Further. It was easily my proudest docking moment aboard Further.

It was such a summery day and I was so stoked about the docking job—AND Schaefer’s diesel price was surprisingly reasonable—that I thought a beer on the waterfront bar would be a good call. Instead, we opted to grab a bag of ice for the cooler and continue on for Annapolis. It would be late when we got there, but we were gonna give it a shot.

Passing beneath the Bay Bridge. Dig how the lights of the cars illuminate the span…

Good thing we did. We FLEW down the canal, now using the current to our advantage and out into the Chesapeake. That same tidal current pushed us down the bay at 8 to 9 knots, and we made it from Schaefer’s to Back Creek in just over six hours. Coming into Jones Cove in the dark, I damn near hit a piling that I’d forgotten about but was able to swing Further’s stern around just in time. And then into her old slip at Stella’s Stern and Keel Marina, the place we’d lived for eight months before going home to Plum Island. And with all due modesty, I stuck that landing too: first try, absolutely fine-tuned her stern into the slip and backed into place on the first try, as smooth as silk. Another proud moment.

Ed and I got Further all secured and then moseyed down the street to Davis’ Pub, for a beverage and a bite of food. We and Further had made it through the best of times and the worst of times, and now I’ll spend more time pondering what’s next.

A friend and former coworker wrote the words that I’ve stolen for the title of this post. And she should know: a health situation while she and her husband are adventuring around the world put the nature of life and time into perspective for her.

It’s a perspective I share—albeit a step removed from what she went through. But I’m 52 and I’ve been dealing first-hand with how short life is since I was 19, and I got another dose of reality last week when I attended the funeral of a girl with who I grew up. It was a sad, tragic story, but just another in a long line of reality checks: my brother dies when he’s 16; a college friend with a husband and kids has an aneurysm and just doesn’t wake up one day; a dear friend from prep school and college, a truly superlative athlete and clean-living person, succumbs to cancer before she turned 50.

So life really is now. And I’m going to resume living mine. Of late I’ve been in kind of a holding pattern, wrestling with questions of what to do with the family home my brother and I co-own, and wrestling with a job search and questions about what I really want to do with my life. After a very positive discussion with my brother this week, I’ve decided to take the plunge and chase my dream.

I’m sailing south to the islands. For real. I’ve had two dreams in my life: one, to live in Alaska; and two, to load up the surfboards and sail away. I did the first (and miss Alaska dearly) and I’m about to go for the second.

The plan is as follows: sail down to Annapolis sometime in the next week to two weeks. I’d like to make it for the gathering of a sailing group of which I’m a member on Sept. 29, but if I don’t, oh well. But I do want to be in Naptown for the U.S. Sailboat Show the weekend of Oct. 6-7. I will once again help my friend with her booth at the show, and I’m also looking forward to seeing my Annapolis friends again. Saturday morning at the Boatyard, gang!

After the show concludes, I’ll hang around Annapolis for a bit, taking care of anything Further needs while I’m still in a place that has all possible resources. Then I’ll spend some time cruising south on the Chesapeake Bay, visiting some of the cool places I missed by not going with my friends Kathy and Renee when they cruised the bay around July 4.

And then I’ll wind up in Hampton, Va., for the last week of October. I’ll spend that week prepping along with 50 or more other sailboats getting ready to head offshore to the Caribbean as part of the Salty Dawg Rally. I currently plan to head to Antigua with the main bulk of the rally fleet, but I am thinking about heading to the British Virgin Islands with a splinter fleet. I definitely want to see the BVIs (I’ve never been there)…AND they have good surf there…AND folks say now is the time to go since they’re still rebuilding after the twin hurricanes last year and it’s still not overrun. But since they’re still rebuilding they don’t have all the infrastructure I might want…AND to get from the BVIs to the Leeward and Windward islands is an upwind slog…AND I’d really like to go spend some time in the French islands around Martinique. So maybe I’ll head to Antigua first, hang out in the eastern Caribbean for the winter and then hit the BVIs on the way north in the spring when it’s a downhill run from down south. Still pondering on this front…

But the point is: I’m going. And that’s where you come in: You can go too. Seriously. I will definitely need crew for any and all legs of this adventure. From Plum Island to Newburyport is a four-day run (a lot of which is motoring on the Delaware and Chesapeake bays if you’re reluctant). Then there’s the cruise down bay to Hampton: funky little towns and quiet creeks AFTER the summer bustle has receded. Wanna go offshore? It’s 10 days or so to Antigua; we’ll head east till we get past the Gulf Stream and then turn south. And for those who just want idyllic anchorages and rum drinks, you can get to the islands from the U.S. in one flight. Hell, from Providence to Martinique is a nonstop flight costing just $250 round-trip.

I’m serious about this last part: one of the reasons I bought Further (as opposed to another boat) is because it has two separate cabins, so even you married friends will have your own private cabin when you choose to come down to the islands and soak up the sun. I built the calendar page on this site so you’ll be able to plan for where you might want to join us. And all I’ll ask you to do is bring some staples with you when you fly down from the first world (peanut butter and such).

Before anyone asks: No, I don’t have the money to do this. I’ve spent a good chunk of my retirement savings on Further and, before that, when I wasn’t working while I took care of my mom and dad. But “boldness has…power…in it,” as Goethe said so I’m taking the leap. And I’ll trust in the universe to provide once I take that leap.

Look, it’s entirely possible that I’ll get down there and, after a winter, decide I’m over it all (I’m definitely verklempt about a winter without hockey…). But it’s also possible that I’ll find I love the cruising life and go even further. Probably the reality will fall somewhere between those two extremes. But I was riding a motorcycle around the hills of New Hampshire a few days ago and I was looking at all the small hill farms and remembering back to when I daydreamed about living happily ever after with my preppy family in a place like that. Well, my life didn’t go that way and then a few days later I attended the funeral of a friend whose life went astray. My life has been absurdly blessed even without a “normal” life in stable, consistent location. But I realized that as nervous as I am about taking such a big leap, I really didn’t want to get to the end of my life and say to myself, “You know, I wish I’d sailed to the islands.” It’s the last really big item on my to-do list (there are tons of smaller bucket-list items). I’d much rather go for it, and if even if it sucks then when I’m at the end of my life I’ll be able to say, “Hey, it didn’t work out but at least I went for it.”

Because, say it with me: Life is now.

PS: There is one caveat to all of this: I continue to explore one potential job that is interesting enough to me that, if it works out and I get an offer, I would accept and resume my career for at least a few years. Don’t hate me for having a pragmatic side.